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Dear Reader, a couple of things. First, you should probably read the first installment of this series to get some background into the characters. Second, this is a story about cross dressing, pegging and some brief male on male contact. If this offends you, don't read it, duh. Also, this is kind of the equivalent second act of a three part play. While it has a fair amount of sex, it mostly provides the transition to the third installment, where there will be a lot more sex, both straight and bisexual, mf, mfm, mm, fmf, etc. All characters are fictional, and over 18 years old. Any inference to people living or passed is purely coincidental.
Thanks for your support.
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"Switch"
Gawd, whenever I heard her say that, my body would twitch (I know it rhymes). I felt like one of Pavlov's dogs, conditioned to respond sexually when she said the word.
I broke away from the kiss with my guy, pulled my dress back in place and turned toward my wife. She kissed me deeply as we pressed together for a moment. I turned and she zipped me back up, then she walked over to the guy I was just with as I walked toward her one night stand lover.
This new guy looked at me like a predator looking at his prey. And, I liked that look. It made me even more feminine and submissive. As I approached him, he started to run his hands over my arms, my chest (and my very expensive fake boobs). Then he turned me around and ran his hands over my back, running his fingers along my bra strap, and further down. He grabbed my ass with both hands and squeezed, like testing the ripeness of a melon. I liked what he was doing.
I don't know about other cross dressers, but when I'm dressed, I enjoy a man taking liberties with my body. I prefer he not ask my permission, just touch and grab the parts he likes. I particularly like hands running up and down my legs. When I'm dressed, I feel my legs are my best feature, and I get lots of compliments on them when I'm in some type of nylons and my 5.5" black patent leather peep toe pumps. This was his next place to explore.
He knelt down and ran his hands over the back of my calves then my thighs. His hands went higher pushing my dress up as he went until his hands were on my ass again, this time under my dress. I was wearing a garter belt and stockings this evening, with my black lacy cheeky panties on the over my garter belt, like any good slut should.
He continued to run his hands over my legs finally standing up, turning me around and unzipping my dress once again. He slipped it off my shoulders letting it fall to the floor. I stepped out of my dress and bent over to pick it up and place it on a chair. As I was bent over, his hands once again went to my ass, this time with a more than gentle slap. I liked that too.
When she said switch earlier, the memories came flooding back to me. My first kiss from a man, my first sucking of a cock, my first spanking from a man, and the first time I was fucked by a man, by Tom to be exact, came flooding back into my mind. It had been a few years ago, but you really never forget your first.
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I woke up in Eve's bed alone. I was a little groggy, some from the drinking, some from the night of sex, which didn't stop once we got back to her place. I remembered the wild foursome we had. I remembered kissing Tom. Not just kissing, we made out like young teenagers on our third date. And, I was a more than willing participant. What the fuck happened to me last night? I didn't regret it, but what were the consequences of my actions going to be. What did Eve think about me this morning?
I was naked as I got out of bed. I wasn't comfortable enough in our relationship to just walk out of the bedroom completely nude in the stark light of the morning. I don't know why. We had spent a couple of hours after we got home enjoying each other's bodies. Anyway, I found my / her pair of panties I wore last night and put them on. It was some amount of modesty, although wearing a pair of her panties might send a different signal.
She was already up and showered, in the kitchen making us something to eat. So, I walked into the kitchen still in her black panties and nothing else. And, there she was, just as gorgeous in the morning as she was at night. No makeup, just a bright smile and an upbeat attitude. She had on a royal blue chemise with a slit up one side. As she bent over, I could see a matching thong. Fuck, I don't know how she did it, but she was always hot effortlessly.
"Morning cute guy", Eve said. I grumbled something as I walked over to kiss her good morning. "Thanks... but go take a shower. You smell like you had sex all night," which was actually true. "I'll layout something for you to wear on the bed when you get done", she added.
I had to agree with her, I probably did stink. I went to the bathroom and turned on the shower. Stripping off my / her panties again, I climbed into the hot water and let it make my body feel so much better. I looked around for shampoo and shower gel and again found everything was very feminine and scented. Duh, what did I think I would find in a single woman's shower, Old Spice? It was the same products that were there the last time I showered here. I shampooed my hair with a very fragrant scented shampoo, and washed with an equally scented body wash. Eh, it's all good I thought. At least I don't stink anymore.
There was a fluffy pink towel waiting for me, so I dried off, ran a brush through my hair and walked into the bedroom. On the bed was another chemise and pair of thong panties. Evidently she decided to up the ante and continue with a feminine theme for me. I immediately thought, hell no, then, what the fuck, if she wants me in fem clothes, so be it. Picking up the chemise, I saw on the tag it was an XL size in pale mauve, kind of purple. It didn't have a slit, but it had a lacy V in front, to show some cleavage. Not so useful to me. The panties, in the same color, were also XL. They were easy enough to put on, and actually felt pretty nice against my showered and sweet smelling skin. My cock and balls fit into the crotch of the thong snugly, so not so bad.
By the way, I may have forgotten to mention my older sister. She was 4 years older than me, and when I was about 5, she used to use me as a live dress up doll. She loved to put me in her dresses, girly shoes and tiaras. We were like little princesses. Unfortunately, my mother loved it. So I guess I was an early cross dresser. She also dressed me as Barbie, and Wonder Woman, Bat Girl, etc. Since I idolized her, it was fine by me. Luckily, that phase only lasted about two years, when she was onto other things. She painted my nails, fingers and toes, and put me in makeup, with the help of my mother. They loved it, so I did too.
I only mention this as things played out later. I must have been predisposed to cross dressing. I mean, most guys would have never agreed to this or at least would have protested much more than I did. The whole thing with my varsity swim suit being basically panties played a part. But I think my sister planted the seed of my allowing, even enjoying being dress as a girl or woman. Anyway, I'll blame her for turning me into a drag queen at an early age. Well, not quite a queen, but a cross dresser.
I walked back into the kitchen and stopped to look again at my sexy... girlfriend??? Maybe we were at that stage. "Very sexy there, cute guy," she commented. "That outfit fits you really well."
"Thanks, I think," I responded. "But what's with the XL size. Did you plan this in your devious little mind before we went out?"
"What... heck no," she laughed. "It was a shipping screw up. I bought it online and the company sent me the wrong size. I did the return thing and got credit for it, but they said just keep it, don't waste the money to ship it back. I was just too lazy to give it away, so, now it's yours, if you want to keep it. It does look good on you."
"I bet you say that to all your cross dressing boyfriends", I countered. She laughed and said "So, you're my boyfriend now, really. Are you sure you're not my 'girlfriend'." She used air quotes when she said that. "And, are you admitting you're a cross dresser now?"
"One night wearing panties does not a cross dresser make" I stated, putting left hand on my hip, cocking it to one side and running my right hand over my head like a diva. "Said as he stands there in a cute chemise and thong panties", she laughed. "Well... there is that," I responded. "I'm hungry, by the way. Whatever you've been cooking out here smells delicious. That workout you gave me last gave me a huge appetite," I said.
"Then let's eat this feast I've prepared," said Eve.
I must admit, it was a pretty good feast. She had prepared a quiche with bacon and English muffin, plus gourmet coffee. Luckily she had made plenty, because I was ravenous. We chatted about nothing and everything until I cleared the dishes and cleaned up the kitchen. She was current on lots of subjects and certainly could hold her own in a conversation. I mentioned earlier, and I understand this is probably sexist, but most of the really attractive girls I ran into couldn't carry on a decent conversation. Eve was really smart, smarter than I was for sure. And I was a straight A student in high school. As we sat for a second cup of coffee, the mood changed.
"Did you have fun last night?" she asked.
It was such a simple question. The answer was very complicated. I wasn't sure how to describe all of the feelings which ran through me all through the night. It had been by far the most exhilarating, sexually arousing night of my young life. So, I just told her what it was for me.
"All of it?" she asked. "Even kissing Tom? It did look like you found that enjoyable."
"That was scary, I have to admit. I've never considered kissing another man, but with you and Carol looking at me... while you were making out with her... I guess I just went for it. I figured it could be a turning point in our relationship, for better or worse. Once we started, I kind of got into it. I'm not sure what would have happened if you hadn't said 'Switch' when you did."
"Tom probably would have pushed your head down to suck his cock... or he may have tried to fuck you. You're not the first guy Tom's played with, I can assure you. But, there aren't a lot of them, from what Carol tells me."
"Wow." I was trying to wrap my head around those possibilities. I'm not homophobic by any means, I've just never considered myself to be... a what, a bottom, a submissive? The guy who sucked me off in high school had actually wanted me to fuck him. He did have a really nice looking ass, but I wasn't there... yet. As he sucked me, he pushed a finger up my ass. Then two. I don't like to admit it, but I really like that sensation.
"Hello, earth to Robin," Eve said. "Where did you just run off to in that pretty head of yours?"
"Sorry. I was just trying to get my head around the possibility of those options you just gave me. What would you have thought if he tried to push me into sucking him, or him fucking me? Would you think I was some kind of twink, a boy toy? Isn't that pretty gay stuff?"
"Well, given what you and I did after we got back here, at most I'd probably say you were bi. I'm bi, so I don't see what it's a problem. I'm not one to throw stones, or be a hypocrite."
"Well then, I admit I did like kissing Tom, once we got into it. I don't know how I would feel about the other stuff, but... well, I don't know."
"We can deal with that another time." Eve looked at me as if she were studying my face, then she said "You have very high cheek bones. It's more of an androgynous face. It's a very handsome or pretty face. I really like it."
"Thanks, I think. No one has ever mentioned it before."
"Well, no one has ever probably taken the time to really look at your face in that manner. Do you mind if I try something? It won't hurt, and you can just see what I go through to get ready for you every time we meet."
"Sure, as long as you're not giving me a tattoo. Not that there's anything wrong with that," I answered.
Eve grabbed my hand and pulled me into her bathroom, got a stool for me to sit on and sat me down. "I want to see what you look like with some... added enhancements." She turned me away from the mirror and began fussing with my face.
I'm sure you've heard this before, but I have to say it was very interesting seeing the sheer number of items she used on my face. At least I counted foundation, concealer, eye shadow, mascara, eyeliner, lipstick, blush, highlighter, bronzer, and setting spray. And there were a few other items I didn't know what they were. The whole process took around 45 minutes. Then, before I could turn around and look, Eve took a wig from her closet and put it on my head. Then she took another few minutes playing with my new "hair" to get it "just right". Her words.
I'm sure probably every cross dresser wannabe goes through this process for the first time. Waiting for the reveal.
Oh my fucking gawd. My jaw dropped. I literally didn't look remotely like the person I'd seen in the mirror for my entire life. I would not have recognized me if I had seen me on the street. Literally if I'd walked up to the person in the mirror, I would not have guessed it was me. I would have looked, probably done a double take at the really attractive woman before me. It's amazing what a relatively small amount of product can so drastically change a person's total look.
"Holy shit!" I said. "What did you do with Rob, and how do I get this chick's number. She could be your sister."
"So, you like?" she asked. "I think you look fantastic as a woman. As I said, you have a very handsome, or pretty, face. I thought you might look hot with some help. And the blond wig sets off your complexion really well. You look very sexy wearing that outfit too."
I just stared at myself, turning to one side then the other. I stood and looked in a full length mirror. I could not reconcile the person in the mirror with the body I thought I had for all my life. It was like I was looking at someone else through a window whose actions were mimicking my movements. It was unbelievable.
"Go lay on the bed," Eve commanded. "Lay in a sexy way, do something sexy, look like a model."
"What?" I asked. "I'm a guy. I've never laid down on a bed in a sexy pose. And why would I do that."
"Because... I asked you to." Well, there was that.
So I got on the bed and laid back on my right side, propping my head up on my right hand, my moving my left hand to my hip. I smiled at Eve. Who quickly took my picture.
"What did you do that for?" I asked.
"I want to send it to Tom," Eve countered. "He asked for you to wear sexier panties for next time. I was going to ask him if he thought this was sexy enough."
"The fuck," I yelled. "No fucking way you're sending him a pic of me dressed like this. Full stop, absolutely NO."
"Come on, don't be like that," she said. "Tom wants to play with you and you know it. He might want to do a lot more than just kiss you, and I think you'll let him. And, if you don't, it will be just a hoot anyway. Carol will think it's funny too. Me thinks thou dost protest too much."
I didn't know what 'dost' think. Whoever dost is. This woman was rearranging my brain. I knew I was more slightly built than a lot of other guys. I knew both women and men were attracted to me. I knew I wasn't homophobic. But, was I bisexual? And, moreover, was I a cross dresser? I knew when I was competitively swimming that my 'suit' was nothing more that panties, actually. I knew most guys didn't completely shave their bodies, although it was common in swimming competition. And, wearing her panties hadn't bothered me at all. Now, the makeover had me looking like a really hot girl. Did I really care that the guy I made out with last night would see me dressed like a 'slut'?
"OK, fine," I surrendered. "Send my would be homosexual lover my pic. But, if this all goes up in flames, don't blame me."
Eve jumped up and down, laughing with glee. She sent the pic, then looked at me lustfully and said "Lay on your back and spread your legs, slut." I did what I was told to do. Then I was attacked.
Eve jumped on me, making sure my legs were spread as she ground her pelvis into my crotch. She mashed her mouth against mine and jammed her tongue down my throat. We hadn't had that much experience together, but this was by far the most aggressive she'd ever been with me. And, I fucking loved it.
After a long make out session with long slow deep very very wet open mouth tongue kissing, Eve moved up and straddled my head. She pulled her thong to one side and mashed her cunt against my lips. I sucked on her clit and ran my tongue all over her pussy. This woman was sexually insatiable. I think we had fucked until 2 in the morning, and now at noon, she was ever hotter. My gawd, what did I get myself into.
Eve ground her pussy all over my face till I'm sure my wonderful makeup was all fucked up. She came at least twice while I ate her, then she slid down my body, pulled my thong to the side, pulled out my throbbing cock and impaled herself on it.
"Fuck me, bitch," she yelled. "Fuck my cunt you faggot bitch. You're my lesbian lover now. Use your big clit to get me off."
WTF. Unleash the kraken. Or whatever legendary monster you can contrive. She was on fire and all I could do was hang on and not be consumed. I tried to hold off for as long as I could. But the whole morning of escalating sexual innuendo, homophobic discussion and cross dressing caught up with me. I could not hold back any longer. I fucking came in buckets.
I laid back on the bed exhausted, and immediately Eve has straddled my face and planted her cream pie on my mouth. She was so cranked up and aggressive, I just opened my mouth and started licking my cum from her cunt. She was thrashing about again and soon my face looked like a glazed donut, covered in sperm, saliva and girl cum. Which got me hard again.
Eve saw my cock standing proud, moved back and impaled herself on my erection. Back and forth she road me for what seemed like 30 minutes, cumming repeatedly until the warmth of her pussy and her gorgeous body took their toll on my and I came a second time in less than an hour. She came again as I filled her, then slumped on my chest and sighed.
"That was fucking great, cute guy," she said. "Thanks, I needed that."
"You're welcome. I thought it was pretty fucking great too."
With that, we fell asleep together, for an hour or so. We woke up and realized it was mid afternoon on a Sunday. As much as I wanted to stay with her again, I had a ton of homework and a big test coming up on Tuesday. She had stuff to do as well. We took a shower together making sure we were super clean and, of course, smelling very feminine.
She pulled out another pair of panties, these were lacy and pink, told me to put them on and wear them home. Eve had me keep the original pair and the chemise and wear them to bed one night this week. I promised I would, thinking hell no, well, probably not, or maybe. I had to be careful when I did my laundry next time, with my growing fem apparel.
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Next week at rugby practice, Tom made no mention of our last meeting or the pic Eve had sent him. It was just a normal mid season practice. As usual, the team stopped by our favorite bar for a couple of beers. The bar owner was a club sponsor so some of our gear had the bar's name plastered on it. Rugby isn't a particularly expensive sport, but there are still costs to cover, especially travel. And, we had an overnight travel game coming up in about a month.
After wolfing down a burger and some fries, I finished my beer and said my goodbyes to my teammates. Just as I was about to walk out the door, Tom pulled me to the side and said "You really look good in purple." Then he gave me a big shit eating grin and walked back toward the rest of the team.
"Oh snap, what the fuck," I thought. Well, no doubt about it, he'd seen the pic of me in that fancy chemise. What amazed me the most was the erection I was getting, thinking about Tom seeing me dressed, and made up, like a woman.
I went back home and sent Eve a text letting her know Tom like the picture she took of me. I certainly didn't have to tell her which one. She just sent back a big smiley emoji then asked if I could come over to her place the next evening. "Make sure you wear your pink panties," she added. I replied back that I would be there in my sexy panties as requested.
"Do you have something planned for tomorrow night," I asked in the text chat. "I've been thinking about your hot ass the last couple of days. I want to play with it tomorrow. Are you up for that, cute guy, or gurl should I say," Eve countered.
Well, now I was really hard, imagining what she might be planning for me this time. And, I let her know I was getting really horny and had a major hard on issue. "Don't you dare jack off tonight, missy," she scolded. "I want you hot and primed when you get here." "Yes, ma'am," was the only thing I could think to say.
I took a cold shower and studied statistics to get my mind off tomorrow night. It was fine till I tried to sleep, then all I could think about were fingers running in and out of my ass. I even had a dream of some non-descript male fucking me as I was in a party dress as we made out. Waking up with serious morning wood didn't help. As far as my classes went that day, all I can say is I hope they weren't teaching something really important. I was in a fog.
I got home late afternoon and showered and shaved all over, as usual. I washed my ass more than usual, and even pushed a soapy finger inside in an attempt to clean me out. I'd find out later how someone really cleans out their ass for some anal play. Once I dried off, I put on the panties, shorts and a t-shirt, ate some ramen noodles and headed over to Eve's place. It takes about 15 minutes to bike over there, so I was right on time.
I buzzed her number and she let me in. I went up the stairs to her third floor apartment, and once again, I was totally blown away. Her blond hair was piled on top of her head. Her makeup was almost goth, dark and foreboding. Then, there was the strapless black leather bustier with garter straps. Those hooked into black fishnets, which fell into black leather thigh high boots. Tiny black thong panties were there for modesty maybe, put on over her garter straps. Hands on her hips, head cocked to one side, staring at me like a predator. Holy fuck.
"Strip, cute gurl, but leave on your panties," Eve ordered. I naturally obeyed without hesitation. "Are you nice and clean, baby?" she asked. "I think so," I stammered back. "I seriously doubt it. Do you know what an enema is?"
"Yes, of course," I replied. "So, did you do that before you came over?" "No, ma'am, I didn't." "Then get your sexy ass into the bathroom. NOW," Eve ordered.
I marched my ass into the bathroom. Lying by the sink was a large red rubber bag with a hose next to it. I had only thought of enemas as those little bottles from the drug store, maybe half the size of a soda can. This bag looked more like one of those camel packs you use for keeping lots of water for a long hike. And the nozzle looked like it was made for a horse. Holy shit.
Eve came into the bathroom. "Turn on the hot water from the faucet," she commanded. Take that packet of salt and pour it into the bag. Get the water warm and fill the bag full. Then strip off your panties and get into the tub."
I was kind of shaking as I did what was commanded of me. I later thought how funny it was that I never questioned what was asked of me. I just acted like a fucking robot and did what mistress said. Did I just think of Eve as my mistress??? Fuck.
Eve took the bag from me as I got into the bathtub naked. "Bend over," she said. And I did. She hung the bag on the shower head, greased up the tube with some lube (thankfully), and slowly pushed the tube up my ass. Holy fuck that was wild. She opened the valve on the bag, and I immediately felt my ass fill with the water solution. And fill, and fill, and fill. My stomach started to bulge a little, like I was a little pregnant. It kept going and going. I thought I was going to explode soon. And, it fucking hurt. A lot. Finally it stopped.
"Hold it... hold it... hold it..." she went on. Finally the cramping really started to bend me over. "Go sit on the toilet," she said. And I did quickly. Not to be too gross, the there was a 'woosh' as I dumped all of that liquid into the stool. Damn, that was almost like an orgasm, the relief I felt.
"Ok, one more time," she told me. "What???? Wasn't that enough?" I begged. "I want you squeaky clean when we have anal play. So before you come over again, do this three time at home."
So, I repeated the process twice more. By the last time, nothing but clear water was running out of my ass. I was clean. Actually, going forward, I would do this process four times to make absolutely sure I was really clean inside and out. And I always did this before my shower with my femmy soaps. How long had I known this vexing woman, a month, six weeks maybe? Down the rabbit hole I went.
I rinsed off in the shower, using her fem shower gel, dried off and put on my panties again. Eve was in the bedroom waiting for me. She smiled at me and patted the bed next to her, inviting me to sit beside her. I turned to look at her, and she kissed me passionately.
"You know, you're only the second guy who ever let me do that to them," she said. "The first guy turned out to be a faggoty wimp, eventually. Are you a faggoty wimp, cute guy, or just a guy who's sexually curious?"
So, how do I answer the question she just asked? If I yell and scream "I'm not any kind of wimp, faggot or not" it comes off again as my protesting too much. If I laugh it off or make fun of it, she probably won't think I take her sexuality themed games seriously enough. And, I certainly don't want to say that I am actually a faggoty wimp, because I'm not. At least I don't think I am.
I looked her in the eye (which is hard considering how outrageously sexy she's dressed) and said "In the short time we've been together, you've awoken in me more sexual desire than anyone I've ever met. I don't know where this is all going to end up, and I'm not really sure I'll like it all. But, I think I'd like to stay on this journey with you for a while longer."
"That's a pretty good answer. I was hoping you would like to continue our sexual exploration. Can you guess what we're going to explore tonight?" Eve asked.
"If I had to venture a guess, I would say my ass. Are you planning on fucking me tonight?" I asked.
"Eventually, yes. But, first I'm going to tie you down to the bed, spread eagle and give you a nice spanking. Then, we'll see how we can open up your ass for a nice hard fucking. Take off your panties, lay down on the bed, face down, arms out."
I kind of gulped. What the fuck was I doing here? Well, I did know what I was doing here, great sex with as gorgeous intelligent woman. I hoped she wasn't a closet serial killer.
I turn and started to lie down. Eve put a pillow on the bed and told me to lie over it, so I did. There were straps under the bed which I'd never seen before, interesting. She secured my wrists first, my right one first, then the left. I was stretched across the front of the bed as my ankles were strapped in. I pulled on my restraints, and I was, in fact, restrained. But, not uncomfortably so.
Eve began by rubbing her hands over my back, like giving me a massage, and working down my body, skipping my ass and starting at my ankles and working up, working my inner thighs. All of this was giving me an erection, which didn't go unnoticed. Then, SWAT.
"OUCH," I screamed. "Holy fuck that hurts."
"I was wondering if you were going to be a screamer. We can't have that, my neighbors will call the police... again," said Eve. She reached into a side drawer and pulled out a ball gag. I'd never really seen one in person, but watching porn gives you an education. "Open wide cute guy."
I tried to keep my mouth shut, but she pinched my nose really hard, and like magic, the ball gag popped into my mouth. She tightened the straps around my head and said "There, all better. I won't damage you, Bobbie, but you can't be screaming in an apartment complex."
And, the spanking began. SWAT, SWAT, SWAT.... And so on. She varied the pace and switched from left to right cheek. After the initial surprise attack, she didn't hit quite so hard. I yelped out a couple of times, then it kind of felt... good? Seems odd, but just the fact I was naked in her bed with her playing with my ass started to turn me on again. After the initial swat, I had lost my erection, now it was coming back.
I was moving my ass back now against her hand, and she noticed it immediately. "Someone seems to like having his ass spanked," noted Eve. Good thing she was using her hand and not a weapon, like a strap or paddle. The swats had an effect on her too. I could tell she was getting tired or her hands were sore.
"Your ass has a nice pink glow to it now," she said. "I think it's time to explore the inner parts of your anatomy." I saw her reach over to a drawer next to the bed and pull out a disposable latex glove. She made a show of putting it on her right hand, as she was preparing to enter my cavern.
With that, I felt Eve dribble something cool on my ass crack. Using her fingers she rubbed the liquid up and down my crack, then slowly rotated a finger over my asshole. It felt pretty good, especially when some of the cool liquid got on my fiery ass cheeks. She'd had her fingers in my as before when she blew me, so this wasn't new territory.
Soon, she put some more lube on ass, and slowly started to push into my body. This was the first time I had ever been penetrated without having my cock sucked. A couple of the wilder girls in high school had done it. The gay swim team guy had done it. And Eve had done it. But all while sucking me off. This was a new experience. And, all of those other times it had been a single finger. I took a deep breath and tried to relax as her finger worked its way inside of me.
I started to moan into the ball gag. "What's that Bobbie, you want more fingers in your ass?" Eve asked. I nodded trying to say yes, when she pull off the straps to the ball gag and I spit it out. "Yessss, please," I answered.
"Here you go, baby," she said as she pushed another finger up my ass. I moaned again as I felt my ass being stretched open. When I watched porn where people were getting ass fucked, the person getting fucked always seemed to be moaning, as if they were enjoying it. And, it didn't matter if it was gay or straight, real cock or strap on, the receiver always seemed to enjoy the experience. I never really watched BDSM porn, or rape porn, so I don't know about that stuff. But the consensual anal sex looked to be pleasurable for the person getting fucked.
As my ass opened up, it felt better all the time. Eve added a third finger and started twisting them around in my ass. There was an initial jab of pain, but it only lasted a few seconds before the pleasure started to take over. I was feeling pretty good when she pulled out her fingers, making me wiggle my ass back trying to get them back where they belonged. Her hands were relatively small, so she put the four fingers of her right hand together like a cone and tried to push them into my body.
Oh my gawd, I thought, she's trying to fist me. I'd seen that on porn videos, and it never looked like something I wanted to try. Luckily, she only pushed them in a little and twisted them around, really reaming me open. She pulled back and I sighed in relief. No fisting for me, yet.
Then, I felt a larger cooler digit pressing against my asshole. I realized it was a dildo, and she was slowly pressing it into my body. I was pretty stretched out, but it was definitely bigger than her three or four fingers. I could feel her twisting it and turning it as she tried to cork screw it into my ass. It took a while for me to adjust to the feeling, but I started to push back against the 'cock' going into my ass. That thought, a 'cock' going into my ass, was like a lightning bolt to my brain. I was taking a cock in my ass. Was my 'girlfriend' trying to turn me gay???
I had to verbalize it. "What are you doing?" I asked. "Are you trying to see if I'm gay?"
Here's where the acronym FOTFLMAO comes in. Eve literally stopped probing my ass with the dildo as she fell over in laughter. "No, you dumb ass," she answered. "I'm trying to see if you like getting fucked in the ass. Liking to be ass fucked and being gay are two different things. You can enjoy receiving anal sex and not be gay, Bobbie."
Well, fuck. She's right again. I let my 'manliness' get in the way of a really good sexual feeling. "Yea, I get it. Please keep going. It's starting to feel really good."
And, Eve kept going. She fucked me with the dildo for about an hour, or really ten minutes. Then she untied me and had me flip over on my back. She wanted me to watch her as she got into her strap on harness, with a slightly bigger dildo, one with a thing which rubbed her clit. She slathered lube all over it, hoisted my legs up onto her shoulders and looked me in the eye.
"So, Bobbie, are you ready for me to fuck you?" Eve asked. "Do you want me to fuck your brains out, like you do to me?"
"Yes, please, ma'am," I squeaked. "I want you to fuck me. Please fuck the cum out of me."
Eve put the head of the dildo against my asshole and slowly started to push. I was panting as I tried to relax. This was a first. My real girlfriend was going to take my anal virginity. We hadn't had any kind of ceremony, but it felt to me like a wedding night, which is odd since I had never thought about getting married before. But, I certainly was losing my virginity. I know there would be a lot of other firsts in my life, but this felt like a big one.
I felt the cooler sheets under my warmed up ass. I felt my finger tips as they glided over her shoulders and back. I noticed the look of lust in her eye as she started to push in. I heard the sounds of birds chirping outside of her windows. I heard the AC kick in. All of this was loaded into my brain as her 'cock' pushed passed my first line of defense and into my body. I was getting fucked. And... I loved it.
Once Eve bottomed out in me, she leaned down on my chest and kissed me, really really kissed me deeply. I kissed her back and grabbed her ass and tried to pull her deeper into my body. She responded and started to fuck me harder. I can go on about how we kissed and I moved my ass and she pounded me harder, but eventually, she pushed in really deep and I erupted. Not had an orgasm, I fucking erupted like a volcano. And, I hadn't even touched my cock. My cum was everywhere between us. And then, Eve came too. Screaming.
"Do I need to put a ball gag in your mouth?" I asked her. "Maybe," she answered.
I stayed there on my back as Eve lay on top of me, catching her breath as I caught mine. It was without a doubt the most intense orgasm I had ever had. It was mind altering. And her 'cock' was still in my ass.
"Are you ok?" Eve asked. She had a concerned look on her face. "I'm great," I panted, quickly reassuring her. "That was unfucking believable," we both said at the same time. Then we both laughed.
We rolled off one another and took in some deep breaths. Wordlessly, we got up and went into the shower. We cleaned each other up, dried off and put on the baby doll night sets Eve had laid out. Hers in royal blue, mine in pink, of course. Evidently she had gone shopping and bought me more lingerie. We went into the kitchen and got glasses of pinot noir.
"Ray, my landlord is coming over for his usual every other Saturday morning visit this weekend," Eve said. This kind of turned the upbeat feeling we just had to a downward trend. I knew she needed help to afford this upscale apartment, and I knew I couldn't afford to help her out this much, but sharing her for rent seemed beneath her. But what could I say, she wasn't my wife and I didn't have a space for us to share.
As she explained it to me, Ray was like a roommate who shared the expense of the apartment. The difference was he only stayed in the apartment two hours a month. And, he was hung.
"I'd like him to meet Bobbie," she stated. My eyes grew wide and I looked at her like she had three heads. "What do you mean you'd like him to meet me?" I asked.
"Not 'you' you, but you 'Bobbie'," Eve said. It took me a few seconds to compute what Eve was saying. "So you want your landlord lover to meet your cross dressing boyfriend?" I asked. "No, I want him to meet my really sexy girlfriend, 'Bobbie'," Eve stated.
I took another minute to ponder what this new revelation meant. Why in the world would she want me to meet her landlord / john / illicit 'sex help cover the rent' partner whatever that's called. So I asked, "Why do you want me to meet this guy, and why would you want me to meet him as a 'girl'?"
"Well... I think you really look hot as a woman, and he's, for better or worse, a part of my life for now. I know I'm enabling his cheating on his wife and that does bother me. But, he's really good in bed and there's no way I could afford this place without his help. I think I would like him to see I have a 'girlfriend' who accepts me for what I am. I'd have you meet him as your guy self, but I think that would freak him out."
"So... am I supposed to watch you two fuck?" I asked.
"Not that. I'd introduce you as my old high school friend who had to come here for an event and was staying with me. You could say 'hi' and then either go to the other room or take off and go somewhere else."
"You know I've only been dressed once, and only in lingerie, and never been out in public. So, I'm saying I might be OK meeting him while dressed, but let's practice it a couple of more times and, I can't believe I'm saying this, but actually go out in public before I try what you're talking about."
"Wow, you'd really let me dress you up and take you out in public? I was thinking about doing that, but I thought I would have to beg and plead to get you to say yes."
"You can still beg and plead with me and promise me 50 blow jobs or something to get me to do that for you."
"That's dumb. Assuming we stay as boyfriend / girlfriend for a reasonable amount of time, I'm going to suck you off more than 50 times. Probably not in the next month, but eventually," Eve said, with a big smile on her face. I had a big smile on my face too. "Let's start now."
I took another shower as Eve got the makeup gathered that she was planning on using on me. This was going to be a tutorial where she started teaching me how to go about getting dolled up enough to pass as a woman. And, not just pass, but to look really hot. Let the makeover begin.
An hour and a half later, I once again looked like a really hot woman, once she added the blond wig. Well from the neck up. Eve brought out a shopping bag and dumped the contents on the bed. It was a bunch of lingerie it a variety of colors. All of it in really shiny white, black, pink and, of course the mauve colors. It all looked really sexy and expensive. And, it was all in my size. There were a couple of pairs of pads which were for inserting into the bra, falsies. I put on the black first, bra and panties with the pads. I looked pretty good.
"I have a top and skirt that I think you'd look really good in, Bobbie," Eve said. The top was lacy and you could see the outline of the bra through it. The skirt was short, like mid thigh, but not trashy short. Then she brought out one last box, a shoe box. The shoes were black patent leather peep toed pumps with a 4" heel. They really looked sexy, assuming I wouldn't break and ankle. I stepped into them and immediately felt like a super sexy woman.
I wobbled around a bit, but surprisingly, I could move in them. I certainly needed to practice so I didn't look like a guy in woman's shoes, but that was just time. I felt pretty good. And, added benefit, my legs looked fantastic. I had a lot more definition in my legs wearing heels. I totally understood why women wore them now.
"Babe, you know I'm bi. If I met you out in a bar, I'd be like all over you. You are sooo fucking hot. I really want to eat your pussy right now, I mean, if you had one."
"Eve, if I met me at a bar, I'd be all over me. I'd want to fuck my brains out."
I strutted around Eve's apartment for a while, sitting with my legs cross like a proper lady, then vamping it up and flashing my panties. This was fun. I had boobs, a nice ass and killer legs. On top of that, I was pretty, I mean really pretty. Damn, I thought, I if I had one more X chromosome instead of that stupid Y, I'd be getting laid every night. That's dumb I thought. I could probably get laid every night as a guy. I was 'cute guy' after all.
What the fuck was I thinking? I didn't really want to be a woman full time, but, I have to admit, if I had an alter personality, this would be pretty hot. As I was strutting around, gazing at very sexy 'woman' in the mirror, something in me changed. I had never thought about dressing in women's clothing, but... looking at that 'woman' I'd become, I was really turned on. My cock strained in my panties, as I thought of myself as a female. I wasn't ready to admit it to Eve, but I really liked being a super sexy bitch.
I had no idea where she was going with this, but I knew I was going to stay with her and ride along to see where it went. I was pretty sure the future was going to involve me playing with some man, or men. Eve seemed keen on my being bisexual. I thought of Tom kissing me. If I was honest with myself, I liked it, a lot. Again, I wasn't about to admit it to Eve, but it was pretty hot, once I got passed the initial shock.
"Let me get dressed and we can go out clubbing," Eve suggested. "What, oh hell no," I countered. "Why not?" she asked. "You are certainly passable and look really good. We could probably pick up some guys, maybe girls and have some fun."
"Yes, Eve, that does sound like it might be fun, eventually," I admitted. "But, look, you've just really fucked me for the first time and now given me my first real total makeover and you've done a fantastic job. I agree I look pretty hot and passable, physically. But... I'm in no way mentally to go out in public like this. I'd probably throw up the moment we went into a club and some guy talked to me."
"You've got it in your head that I'm a cross dressing bisexual guy whose ready to have sex with the first hot guy I meet. I really like what you've done with my body, and I'm sure I will attract a lot of male attention eventually. But I'm not ready mentally for that. You've just fucked my ass, and I liked it and want to do it again, with you. I don't know if I'm ready for some guy to ask me to dance, to kiss him, let alone to suck his cock, or gawd forbid let him fuck me."
"How about this, we tone down the makeup a bit, I leave on the sexy undies, put on a pair of skinny jeans and a sweatshirt and we go out and get something to eat at like an Olive Garden? Let me get used to the idea of people seeing me as a woman before we dive into the whole pickup thing."
"OK, OK, fair point," Eve said. "I'm just really amped up since you look so fucking fuckable. I think it would be hot to see some stud nail you while I was getting it on next to you. We could kiss and hold hands as we got fucked."
"Damn girl, slow the fuck down," I replied. "I'm not saying no to that possibility eventually, but let me get my feet wet first by just walking around the mall as a woman. Maybe getting something to eat, maybe shopping then back here later. This is really exciting, but I'm also really scared. I've just found out I can look really good as a woman, let me get used to the idea before we push it too far."
Eve agreed, and she redid my makeup to a more casual everyday kind of look. She did have a pair of yoga pants which would stretch just enough for me to fit into them. And she had a kind of baggy sweatshirt I could wear. My running shoes were generic enough to be worn by either sex, so that was fine. When we were done, we looked like a couple of co-eds heading out for a casual evening.
As we approached the door, I kind of froze. Gawd, what was I doing. Did I let this go too far? Then I looked in the mirror again, and saw two attractive women going out shopping. I looked at Eve's face, and she had a smile the proverbial a mile wide. She seemed elated that we were going out as girlfriends. So, what the hell, it's not like I'm going to be arrested for dressing like a girl. We walked out into the world, like I was a newborn woman, entering humanity for the first time.
Eve wasn't a wave slowly pushing me forward into cross dressing. She was a fucking tsunami, a force of nature. I could see why some guys would be put off by her. She wasn't a femdom type of woman, but she had a strong will and knew what she wanted. And, it wasn't like she was humiliating me, she was encouraging me to explore my feminine side. And, I loved the way I looked as a woman.
Eve drove us to the mall on the far side of town, not frequented that much by kids from the university. And, to my surprise, 99% of the people didn't give me a second look. Some guys would look at us and one guy did whistle, like an idiot, but basically it wasn't a big deal at all. Eve insisted we buy me another pair of shoes, casual wedge sandals with a low heel. Nothing too sexy, and insisted I wear them instead of my running shoes. We bought me a couple of pairs of panties and bras, and a skirt and top.
We ate a light dinner at the food court and decided to head home. "You know what we should do?" Eve asked. "We should stop by Tom and Carol's and just say 'hi'. I think it would be a hoot if they saw you like this." "I don't know about that," I resisted. "Oh come on," she pushed. "If you're ever going to have to meet some other people, those two are the least likely to say anything negative."
She had a point. We probably would never find a more friendly audience. "Fine," I relented. Damn this girl likes to push things. And I did say I wanted to be along for the ride, so, fuck it. Let's see what our friends say when they see me as a woman.
We headed to Tom's apartment, where Carol was typically there. Eve texted Carol saying she wanted to stop by for a minute and show her something she made. Carol texted her back and said they were going to be there for a while longer and come over.
We parked in the rear of the complex, walked up and Eve knocked on the door. Carol opened the door, dressed casually like we were and looked at me then Eve with a questioning look.
"Hey, Carol, how you doing," Eve asked. "Great, thanks, uh, who's your friend?" Carol asked. "This is a friend from my high school. She's in town passing through and stopped into say hello," Eve answered. "Her name is Bobbie."
I extended my hand and Carol shook it. "Nice to meet you," we both said at the same time. I tried to raise my voice a couple of octaves to sound more feminine. "Come on in," Carol invited us.
I walked in and saw Tom in the kitchen opening a bottle of wine. I stood and waited to be introduced to Tom. "Hey Tom, this is my friend Bobbie from high school," Eve said. Tom gave me a once over look, like evaluating a piece of meat, or, like all men do when they see and attractive woman. I extended my hand to Tom. He took my hand, pulled me in and gave me a small hug, nothing overtly sexual, but more than a casual greeting.
"Hey, Bobbie, any friend of Eve's is a friend of ours. Welcome to our humble abode. Would you like a glass of wine, ladies," Tom said. We all nodded and he went to get the wine and some glasses.
We sat down and Eve and Carol started chatting as I sat there and nodded occasionally. I would answer some simple questions with yes or no, as the conversation went on. Tom continued to look at me, like he was trying to figure something out.
Finally, Carol asked "So what was this thing you made that you wanted to show me?" It was time for the big reveal.
"Carol, Tom, this is...(drum roll)... Rob," Eve said, with a tada added at the end. "Look what I made all by myself. Well, with some help from my subject."
"Hi guys," I said in my regular male voice.
"What the...," Tom started to say. "No fucking way," said Carol. "Way," said Eve. I stood up and did a pirouette then struck a pose with my hand on my hip.
"With that wig on and the makeup, you really are a totally different person," said Carol. "I can see the male Rob I know, but only if you'd told me. He does look something like the picture you sent us the other day, but this is like a 3D version. Fantastic job, Eve. You've created a masterpiece."
"Amazing," added Tom. "I thought she, err, he looked familiar, but I wouldn't have guessed it was Rob. Way to go, guys, you fooled us, like the TV show."
We continued the discussion of my conversion to a woman as we finished the bottle of wine. Once it was done, Eve stood and said "Well, we hate to drink and run, but I'm taking Bobbie back to my place and I'm going to fuck her brains out... again." That got a huge laugh from our friends as Eve pulled me up and grabbed my ass.
As we said our goodbyes, Tom walked up to me, grabbed me and kissed me on the mouth again. And, I didn't resist in the least. I opened my lips to let in his probing tongue. I put my hands around his neck, and he put his hands on my ass. He pulled me in tight, and I could feel his erection as we made out. Once again, I found I really liked being kissed by Tom. After about a minute, Eve stepped in. "Enough you two," Eve chided. "She's mine tonight. Maybe you can have her later."
"Count on it," said Tom.
When we got to the car, Eve pushed me up against the car and kissed me deeply. "You know, as soon as he gets the chance, Tom is going to fuck you."
"Oh fuck," I replied. "I know you're probably right. I could see it in his eyes as we were chatting. He was undressing me when he thought I was a girl. And, I think it got worse when he found out who I really was."
"As a woman, you are very desirable. I'm sure you realize that. Do you want to continue with this and see where it goes, or do you want to stop it, maybe save it for Halloween?" Eve asked.
"I'm not sure," I answered. "But right now, I want you to take me home and fuck my brains out, like you told them. This has gotten me so horny, I need your 'cock' in me."
Eve did in fact take me home, stripped me to my bra and panties, and fucked me as she stuffed her tongue in my throat. I moaned and cried out as she pounded my hot boipussy until we both came hard. When she finished with me, she pulled out a butt plug with a jeweled end and pushed it into my ass.
"This will keep your ass nice and open so I can fuck you whenever I like," Eve said. With that, we fell asleep, spooned together.
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I missed Eve's meeting with Ray the next day. It was just too soon for me. Sooo... the following two weeks were filled with me being fucked on a regular basis. Eve came up with idea of equity, for every time I fucked her, she would fuck me. This became kind of an approach / avoidance conundrum, because I really liked fucking Eve. She was diligent about making it a total equality situation. Then she changed it to a two for one thing. I fuck her once in her ass, she fucks me twice.
If I fucked her while she was made up or dressed in sexy lingerie, I was going to be dressed up and / or wearing sexy lingerie. As a side note or benefit, I really got used to being dressed and made up and getting fucked. I'll admit Eve's fucking me was getting more enjoyable. I actually had orgasms most of the time just from getting fucked.
Sometimes when we dressed up, we'd go out to dinner then back home to fuck. On Wednesday of the second week, we dressed up pretty hot, short skirts, snug tops, low heels, and went to a bar for drinks. A couple of guys hit on us, be Eve told them we were lesbians, so they left us alone. Damn, that was actually pretty fun.
The other thing was oral sex. Not only was I supposed to eat her pussy till she came, I was also 'made' to suck her 'cock' before she fucked me. She was training me to deep throat a real cock. These became pretty intense training sessions. But, I was making progress and could almost take her strap on all the way down.
Finally after two weeks of this continued sexual 'training' it kind of came to a head. Her rent help lover was coming over in the morning and Eve wanted Bobbie to meet him. After teasing and edging me again for a long time this evening, I agreed. In the morning, she had me dress as a sexy, but subdued co-ed, with a low cut top and sexy boy shorts, showing off my ass. And the wedge sandals she bought for me earlier.
Eve was dressed in white very sexy lingerie, lacy bra, garter belt, white stockings, white heels, and thong panties. Over this she wore a sexy kimono style robe, with her make up looking perfect. She looked like a geisha ready for her man. Well, she sort of looked that way to me.
Ray knocked on the door precisely at 10am. Eve let him in and I was surprised to see how large he was, and black. I had seen him before, but only in passing. They kissed, which churned some resentment in me. Eve turned and introduced me, 'Bobbie' to Ray.
"Bobbie, this is Ray. He's my 'friend' and really helps me out with my college finances," Eve said.
"I bet he does," I thought. But I said "Nice to meet you, Ray. I'm about to head out to run some errands. You two have fun while I'm gone."
With that, I left them, feeling Ray's eyes checking out my ass as I closed the door behind me. I walked over to the coffee shop across the street. I ordered a latte and found a table with a view of Eve's apartment. At that time on Saturday morning, there weren't too many other students wandering around. And most of them were nerds, not the people I usually hung with.
I took out my phone and acted like I was looking at something, which I was. It just wasn't on my phone. Within a few minutes, I saw movement in the sliding glass door to the patio off Eve's apartment. I saw Eve, without her kimono, standing facing the window. Ray must have been standing behind her, because I saw two brown hands reach around and grab her tits over her bra. The hands massaged her tits for a bit, before slid out of view. Eve seemed to have her head back, lying against Ray's shoulder.
A few seconds later, her white bra slipped off her shoulders and fell to the floor. Anyone could see Eve was naked from the waist up, if they focused on the glass door enough. I don't know who else was watching this, but I was transfixed on the site before me. Once again, the brown hands moved around and grabbed her tits from behind. Ray seemed to be pinching her nipples.
Jealousy and arousal ripped through my body as I watched another man 'using' my girlfriend. I'd watched Tom fuck her before, and I knew we weren't monogamous, but, damn, this was crazy. Someone could have robbed the coffee shop right now and I wouldn't have noticed. I was kind of angry and really turned on. I was getting an erection in my panties.
I was almost breathless as I watched my girlfriend being manipulated a couple of floors above me. Ray's right hand started to move down slowly finally reaching Eve's panties. He slowly eased his hand into her panties and further down, until he reached her pussy, is my guess. It was not clear, but he seemed to be fingering her pussy.
Eve's hands dropped to her side, not to stop Ray from what he was doing, but to push her panties off her hips and down to the floor, joining her bra already there. With that move, they pulled back from the glass and moved further into the apartment. I was left to sip my latte with a hard on and wonder what was going on in the apartment. But, what the fuck, I knew what was going on, at least in the macro sense. They were fucking.
From what Eve had said before, Ray never stayed more than an hour. Whatever bullshit he gave to his wife, the meeting never went longer than the one hour time limit. So, for the next fifty minutes, I sat at the table, my mind going between rage, lust, fear, hunger, excitement, craving and desire. I could only imagine the carnal things happening in that apartment. I wondered what his cock looked like sliding in and out of Eve's hot cunt. I wondered how many orgasms she was having and if he was a 'one and done' kind of guy. I also admitted to myself that I wondered what his cock tasted like. Would I be able to take it up my ass?
Finally, I saw Ray emerge from the apartment building and walk the other way. He looked very happy.
I got up and immediately ran up to Eve's apartment. The door wasn't locked, so I walked into her bedroom. Eve was lying on her bed with her legs spread wide looking me straight in the eyes. "Eat me," she demanded. And, I did.
She had cum running out of her pussy, lots of cum. I pushed my face into her cunt and started lapping up all Ray's offering. "Yessss...," Eve hissed. "Lick up all of my lovers sperm. He fucked me really hard and deep. There's a lot of his cum in me. Eat all of it, Bobbie." After a few minutes, Eve changed positions and sat on my face, pushing more of Ray's seed into my mouth. I ate all of it. Eve had another tremendous orgasm as I sucked on her clit.
"Strip down to your bra and panties," Eve commanded. And, I did. She rolled over next to me and started to rub my cock. "Pretty hot, wasn't it?" I could only moan as she was playing with my body.
"Did you like watching Ray kiss me?" she asked. "Did you like watching him strip me? Did you like seeing his hands on my body?"
"I didn't get to see much," I answered. "I was so... jealous, angry, aroused. I got hard as a rock."
"Do you want to see more? Do you want to see his cock slide into my pussy? Do you want to hold his cock and guide it into my pussy? Do you want me to hold his cock and guide it into your ass?"
Fuck. She was driving me nuts. I was sooo turned on and sooo rock hard now. I would have admitted to almost anything. Damn this woman was like my kryptonite.
"I think Tom should take your virginity," stated Eve. "He's seen you dressed as a woman, he's kissed you a couple of times and, from what Carol says, he thinks you're really hot."
"What makes you think I want some guy to fuck me in the first place?" I responded. "I enjoy being pegged by you, but that doesn't mean I want a 'real' cock up my ass." I knew I was lying to her, trying not to be too anxious to go after cock. It seemed easier to let her take the lead.
"Don't try and give me that bullshit. Why do you moan and say 'yes' when I'm fucking you and I ask you if you want a 'real' cock up your hot faggot ass?" Eve asked.
"I'm just role playing," I answered. "I was just responding to what I know would really turn you on."
"Bullshit," Eve said again. "Maybe the first time, but you can't fool me. I know you want to get fucked for real. And, I'm fine with that. I think you should open your horizons and be more bisexual, like me."
She started rubbing my cock through my panties, getting me harder, if that was possible. Then she was teasing me by just running her fingernails lightly along my shaft over my panties. "You want cock, don't you?" she asked.
"Oh fuck, that feels sooo hot. Don't stop, baby," I moaned.
"Tell me," Eve said. "Tell me or I stop this right now." She continued to lightly caress me, driving me crazy.
"Yes, I want cock. Tom's cock. I want to lick it and suck it. I want to kiss him and make out with him."
"And, get fucked by him?" Eve asked, as she slowly started to stroke my cock, then licking my cock head.
"Oh gawd, yes. I'll let Tom fuck me," I whined.
Eve didn't let up. "Just let him, or beg him?"
"Yes, I want Tom's cock. I want him to fuck me. I'll beg him to fuck my hot tight faggot ass."
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